Abstract
Allylic alcohols can be transformed into γ,δ-unsaturated α,α-dibromo esters through a two-step process: formation of a bromal-derived mixed acetal, followed by tandem dehydrobromination/Claisen rearrangement. The scope and selectivity of both steps have been investigated. The product α,α-dibromo esters were subjected to various carbon-carbon bond-forming reactions, oxidations, and lactonizations.
Publication types
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Research Support, N.I.H., Extramural
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Research Support, U.S. Gov't, Non-P.H.S.
MeSH terms
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Acetals / chemistry*
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Esters
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Ethylenes / chemistry*
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Hydrocarbons, Brominated / chemical synthesis*
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Hydrocarbons, Brominated / chemistry
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Ketones / chemistry*
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Molecular Structure
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Propanols / chemistry*
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Stereoisomerism
Substances
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Acetals
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Esters
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Ethylenes
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Hydrocarbons, Brominated
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Ketones
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Propanols
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allyl alcohol
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ketene